New violet vat dyestuffs



' proved to Patented June 2, 1931 MAXIMILIAN PAUL SCHMIDT AND WILI-IELM'NEUGEBAUER, On'BiE RIoH-oN-THE- REINE, GERMANY, ASSIGNORS, BY IVIESNEASSIGNMENTS, GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y.,

A CORPORATION OF DELAWARE NEW VIOLET V AT DYESTUFFS No Drawing.Application filed. February 23, 1926, Serial No. 90,206. Renewed.October 10, 1927.

The present invention relates to new Violet vat dyestuffs.

The violet vat-dyestufi obtainable according to the process described inBrit. Pat. 201,786 by condensing perylenetetracarboxylic acid witho-phenylenediamine has be unsuitable for dyeing purposes owing to thefact that its leuco compound is very difiicultly soluble. Furthermore,there is described in German Patent Nr. 412,122, Example 6, a dyestuifwhich is produced by condensing tetrachlor-perylene-tetracarboxylic acidwith ortho-phenylenediamine. Although this dyestufl is readily solublein the Vat its fastness to soaping and boiling with sodium carbonate isvery unsatisfactory.

Now we have found. that dyestufis of good solubility in the vat as wellas great fastness to soaping and to boiling with sodium carbonate can beproduced by using for the condensation process such halogenatedperylenetet-racarboxylic acids as contain only one to three, preferablytwo, halogen atoms.

In the description and claims by the term perylenetetracarboxylic acidwe understand not only this acid itself, but also its anhydride.

The followingexample serves to illustrate our invention the parts beingby weight.

46 parts of dichloro-perylenetetracarboxylic acid (obtainable bychlorinating perylenetetracarboxylic acid in chlorosulfonic acid) arewell ground together with 32 parts of ortho-phenylenediamine and themass is then heated first for 34 hours to 130150 C. and then for another3-4: hours to about 260 C. The resulting coloring matter, after beingdried and ground,'may be used directly for dyeing purposes. It forms'abrownish black powder which is soluble in concentrated sulfuric acid toa blue solution and is readily soluble in the vat. The dyestuff gives onI cotton a violet dyeing of excellent fastness f to soaping, boilingwith sodium carbonate, I and also to light and chlorine. It correspondsto one of the following isomeric formulae: v j 1 other Xs stand forhydrogen.

In the place of theortho-phenylenediamine may be used substitutionproducts, homologues or analogues thereof.

We claim:

1. As new products the vat dyestuifs being obtainable by condensing aperylenetetracarboxylic acid, containing' at the most three halogenatoms, with aphenylene-diamine and corresponding most prob-ably to thegeneral formula: 3

'70 wherein 2 Xs' sta-nd for halogen atoms, the p amine andcorresponding lene-tetra-carboxylic acid signatures.

wherein at the most 3 Xs represent halogen atoms, the other Xs hydrogen,and wherein the phenylene nuclel may be substituted.

s new products the vat dyestuffs being obtainable by condensing a'perylene-tetracarboxylic acid, containing at' the mostthree chlorineatoms, with a phenylene-ior-tho dimost probably to .thelgeneralformula;f a

wherein 2 Xsrepresent c'lilorine atoms, the

other Xs hydrogen, formingin a dry state a brownish-black powder,yielding on cotton a violent dyeing'of excellent fastness properties. VIn testimony whereof we hereunto aflix our MAXIMILIANPAUL SCHMIDT.WILHELM NEUGEBAUER.

